sinococuline

ID: ALA524026

Cas Number: 109351-36-2

PubChem CID: 5489400

Max Phase: Preclinical

Molecular Formula: C18H23NO5

Molecular Weight: 333.38

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Sinococuline | Sinococuline|109351-36-2|CHEMBL524026|(6beta,7beta,9alpha,13alpha)-8,14-Didehydro-3,8-dimethoxymorphinan-4,6,7-triol|J5624PB437|(1S,9S,12S,13S)-4,11-dimethoxy-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5,10-tetraene-3,12,13-triol|ALKALOID FK1000|SCHEMBL166476|UNII-J5624PB437|DTXSID00911127|BDBM50260779|AKOS040763319|FK-1000|F92832|Q15427859|Morphinan-4,6,7-triol, 8,14-didehydro-3,8-dimethoxy-, (6beta,7beta,9alpha,13alpha)-|(1S,9S,12S,13S)-4,11-DIMETHOXY-17-AZATETRACYCLO(7.Show More⌵

Canonical SMILES:  COC1=C2[C@@H]3Cc4ccc(OC)c(O)c4[C@]2(CCN3)C[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C18H23NO5/c1-23-12-4-3-9-7-10-14-17(24-2)15(21)11(20)8-18(14,5-6-19-10)13(9)16(12)22/h3-4,10-11,15,19-22H,5-8H2,1-2H3/t10-,11-,15-,18-/m0/s1

Standard InChI Key:  MFKPWBJXKCSPGK-KNORBDTNSA-N

Molfile:  

     RDKit          2D

 25 28  0  0  0  0  0  0  0  0999 V2000
   -2.8403    1.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8389    1.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4120    1.9022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1285    2.3112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4091    1.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1327    0.6635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7039   -0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6994    0.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4205   -0.5761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1354   -0.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8531   -0.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8623   -1.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1475   -1.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4278   -1.4050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5544    0.4310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8479   -1.9826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1555   -2.6350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5503    2.3101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5508    3.1313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0648   -2.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0071   -0.5849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0529    0.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6803   -0.9948    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5777   -1.7960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5533    0.6620    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  5  3  1  0
  3  4  2  0
  4  1  1  0
  5  6  2  0
  5  8  1  0
  6 10  1  0
  9  7  1  0
  7  8  1  0
  9 10  1  0
  9 14  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 10 15  1  6
 14 16  1  0
 13 17  1  1
  1 18  1  0
 18 19  1  0
 16 20  1  0
  7 21  1  0
 21 22  1  0
 15 22  1  0
  7 23  1  1
  1  2  2  0
 12 24  1  1
  2 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA524026

   SINOCOCULINE

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 333.38

Molecular Weight (Monoisotopic): 333.1576

AlogP: 0.58

#Rotatable Bonds: 2

Polar Surface Area: 91.18

Molecular Species: BASE

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.83

CX Basic pKa: 8.77

CX LogP: -0.68

CX LogD: -1.83

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: 2.29

References

1. Carraz M, Jossang A, Rasoanaivo P, Mazier D, Frappier F..  (2008)  Isolation and antimalarial activity of new morphinan alkaloids on Plasmodium yoelii liver stage.,  16  (11): [PMID:18456502] [10.1016/j.bmc.2008.04.033]

2. Carroll AR, Arumugan T, Redburn J, Ngo A, Guymer GP, Forster PI, Quinn RJ..  (2010)  Hasubanan alkaloids with delta-opioid binding affinity from the aerial parts of Stephania japonica.,  73  (5): [PMID:20426456] [10.1021/np100009j]

Source

Source(1):

• Scientific Literature